In Loser Take All: The Comic Art of Woody Allen, Maurice Yacowar traces Woody Allen’s transformation from a “cult favorite into America’s foremost humorist” (1). The turning point of this transformation is generally attributed to the success of Annie Hall. Not only did Annie Hall do phenomenally well at the box office, but it was also nominated for five Oscars and won four, including Best Picture, Best Screenplay, and Best Director, all which could be directly attributed to Woody Allen. Yacowar asserts that just because comedy is lighthearted in nature, there is an underlying seriousness and significance inherent in humor, especially in the case of Woody Allen, which makes it essential to critically study his films. While humor can initially seem dismissible due to its comedic and blithe nature, Woody Allen instills such meaning and honesty in his humor that it often holds more meaning than dramatic counterparts. This humor is apparent in every single one of Allen’s films, although some to a greater degree than others. Allen is able to consistently convey meaning about serious topics such as loneliness, anxiety, love, and existentialism through his humor. Allen also explores the relationship between life and art through this humor, and it is through such humor that the viewer is able to define the meaning and implications his work. Yacowar specifically addresses each of Allen’s individual films and demonstrates how they uniquely use humor to create and communicate deeper meaning. Due to the chronological structure of the book, Yacowar shows how each film influences and leads to the next film in Woody Allen’s repertoire. One major issue in Annie Hall is the blurring of reality and fantasy. Allen makes it difficult to discern to what degree the film is autobiographical and therefore a realistic portrayal of his life and thoughts. This ambiguity is further compounded by his direct addresses to the audience. This blurring of the line between reality and fantasy manifests itself multiple times throughout the film, thereby repeatedly challenging the viewer.